


Tonight's Entertainment

by fawnspotsam



Series: Sex Work AU [1]
Category: Marvel Cinematic Universe
Genre: Alternate Universe - Prostitution, Anal Fingering, Anxious Tony Stark, Arc Reactor Issues, Biting, Blow Jobs, Dirty Talk, Dom!Steve, Face-Fucking, Hand Jobs, Humiliation, Identity Porn, M/M, Post-Coital Cuddling, Prostitute!Steve Rogers, Sub!Tony, Tony Stark Still Has Arc Reactor, Verbal Humiliation, Wrist Pinning, prostitute!Steve, terms of endearment
Language: English
Status: Completed
Published: 2019-02-21
Updated: 2019-03-11
Packaged: 2019-11-01 16:00:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,040
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17870306
Author URL: https://archiveofourown.org/users/fawnspotsam/pseuds/fawnspotsam
Summary: AU where prostitution is legalized and regulated.Tony hires his first male escort. Steve Rogers is a great first, am I right?





	1. First Meeting

**Author's Note:**

> Nothing incredibly explicit in this chapter. Next chapter has the sexy times.
> 
> Not yet beta'd!  
> Also please let me know if I should be adding or changing any tags, in case I missed something or miscategorized something!

Tony tapped impatiently on his phone while he waited for this evening’s entertainment to arrive. He was willing himself not to get too absorbed in any design schematics or SI documents Pepper has been prodding him about.  He wanted to be relaxed.  

It’s not as if he had never hired an escort before. He realized years ago that dating would be incredibly difficult with his lifestyle. He’d never hired a man before, though. He was happy to specify his preferences on the website (height, musculature, hair colour, etc.) but his anxiety was growing as the minutes ticked by, approaching the agreed time of 9:00pm.  

Women Tony usually hired from this service were often his height, brunettes, dainty and dressed in delicate evening gowns with sheer stockings and garter belts that drove him crazy. He enjoyed romancing them for the evening (‘the girlfriend treatment’, they would tease) and taking them to his bed. 

Activities in the bedroom would depend on the company and Tony’s requests that evening. Sometimes he felt like bondage, or pegging, or whatever Tony’s guest picks out of his drawer of toys. 

With men, however, Tony felt ~~scared~~ unsure. He was certain that the agency would follow his instructions, as they have never let him down before, but he wasn’t sure what he might do with a man for the evening. Would they laugh at Tony if he offered dinner? Wine on the couch? Conversation? 

He’s overthinking. He’s always overthinking.  

Tony opens his email to read the confirmation for the tenth time over.  

 

* * *

 

 

 

 

> SUBJECT: Escort Service Order Confirmation 
> 
> FROM:  V.P. Escorts
> 
> TO: Tony Stark
> 
>  
> 
> _M, minimum 6’0”, non-smoker, muscular_  
> 
> _Dress Code: [n/a]_  
> 
> _Activity Requests: Sexual Contact*, Rope Usage, Biting_ _, Dominance*_
> 
>   * _Sexual Contact: Oral_ _Sex, Anal Sex_  
>   * _Dominance: Humiliation, Hair Pulling, Spanking_  
> 

> 
> _Special requests: Overnight Stay, Alcohol Consumption_  
> 
>  
> 
> **Scheduled: 2/20/2019 9:00pm - 2/21/2019 9:00am**  
> 
> SINGLE ESCORT (1) EVENING =   $900.00 
> 
> SPEC REQUEST =   $750.00 
> 
> SPEC REQUEST =   $500.00 
> 
> SUBTOTAL = $2150.00   
>  TAXES =   $322.50 
> 
> TOTAL TO CREDIT CARD = $2372.50 
> 
> _All service requests are subject to the judgment and final decision of Escort Commissioned, in accordance with the_ Sex Workers Protections Act _. Billing disputes must be taken to our_ _Customer Service_ _department. Contact information is listed at the bottom of this email and_ _on our website_ _._  

* * *

 

 

“Sir, your guest from V.P. Escorts has arrived for the evening. Shall he be brought up?” JARVIS’s voice pulled Tony out of his thoughts. He checked the time. 8:55pm.  

“Yeah, J.” Tony left his perch on a barstool at his kitchen island to approach the elevator on his floor.  

The large metal doors opened and Tony’s mouth was agape as the man who he had hired for the evening stepped out.  

He wore dark jeans and a brown leather jacket which hung open over a white button shirt. His shoes matched the leather of his jacket and they shone as though they were freshly shined. His blonde hair and broad shoulders gave Tony a sense of déjà vu that he could not place. 

“You have a beautiful home.” The man begins, smiling at Tony with all the charm of a boy scout. He held out an open palm. “My name is Steve.”  

Tony shook Steve’s hand and smiled, nodding politely at the compliment. “Tony.” With their hands still together, Tony pulled Steve closer to himself and placed his left hand at the small of Steve’s back. “Can I offer you a glass of wine, Steve?” 

They walk towards Tony’s den where Tony has his bar stocked and ready for company. Steve shakes his head. “Do you mind if I opt for a beer?” Tony releases Steve and gestures to a bar stool as Tony walks behind the slim counter to duck into the mini fridge. 

“You are in luck, good sir! A Corona, it is.” Tony placed the cold glass bottle in front of Steve before mixing himself a martini. As he worked on his drink, Steve took only one sip of his own. Tony actively did not gawk when he realized Steve popped open the metal cap with his bare hands, and that... was unfairly sexy.

Tony took a testing sip of his cocktail before setting it down and leaning forward slightly on his elbows. Steve’s eyes were a strong blue and they did not back down against Tony’s gaze. 

“Not much of a conversationalist, are we?” Tony asked with a little grin. Steve chuckled, his cheeks a little pink. “That’s alright, I’ve been told I talk enough for three!” 

Steve reached out to touch Tony’s elbow, just for a quick second, smiling. “Tell me what you’d like to talk about.”  

 

The evening carried on an air of playfulness as they moved to the kitchen where Steve agreed to be fed a ridiculously small amount that Tony would have thought a man of Steve’s size (6’2”? No, he must be at least 6’4”!) would want.  

Steve ingeniously asked Tony about a painting hung above the fireplace in the den and Tony offered to give Steve a tour of the penthouse. Tony had idly collected art over the years from charity auctions and various gifts from businesspeople he’d met with. Steve showed more interest in the paintings decorating Tony’s walls than most guests did, so Tony found himself just following Steve as Steve’s eyes followed the paint strokes and light of the scenes before finding the next piece in Tony’s collection. 

“I don’t have any art in my bedroom, but... would you like to see it?” Tony winked, taking Steve’s second (empty) beer bottle from his hand and placing it on an end table by his closed bedroom door. 

“I thought you’d never ask, Tony.” Steve’s voice was cool, calm. A hint of humour in his inflection, he seemed to enjoy Tony’s delicate approach at this evening’s itinerary. 

A king sized four post bed with dark, soft sheets was illuminated as they entered. The automated lighting made Steve start gently, and Tony smiled. He loved when that happened. Tony led them forward to the side of the bed. He removed his watch and put his phone down on the bedside table. He looked to Steve, who stood by him, watching. 

“Sit, um...” Tony said, and Steve sat gracefully on the edge of the bed, holding his hand up to ask Tony to follow. Tony stared down into Steve’s stupid amazing blue eyes and forgot what he had been meaning to say next. 

“What do you want to do?” Steve asked, hands and eyes still waiting. 

Tony’s mouth was dry, but he willed himself to use words. “Did-Did you read the request form?” 

Steve nodded. “Yes, I did. Would you like to show me your rope?” 

In that moment, Tony felt a pang of fear. “Uh, no. Not yet.” He remembered Steve’s hand. It looked warm, soft, exciting. He settled his hand in Steve’s. He received a gentle squeeze over his fingers. 

“You didn’t specify online, is kissing good?” Steve asked, blinking. Tony nodded quickly.  

Steve slid his hand from holding Tony’s palm, hooked their thumbs and pulled him down by his wrist. Tony’s lips met Steve’s in a breathy rush, Tony’s teeth catching Steve’s bottom lip and dragging back as they opened their eyes. “Very good.” Tony whispered, pushing with the wrist that Steve was still holding to drop Steve gently onto his back. 

“Your first time?” Steve asked, kissing Tony again softly when Tony climbed over him slowly, planting an elbow by Steve’s shoulder for support. 

Tony laughed, shaking his head. “Oh, god no. I’ve been doing this a long time.”  

“Well, sweetheart, you play it off like you’re a blushing bride and it’s adorable.” 

It is absolutely not fair that Tony was made to blush at that.  

Steve’s free hand rose to touch Tony’s thigh, sliding up to grab a handful of his ass. Tony let out a small gasp, shivering as Steve’s fingernails dug in as he squeezed. “Good, good.” Steve whispered into Tony’s ear as he squeezed his wrist trapped between their chests. 

Tony keened downward, melting against Steve’s warm body. He was growing hard and he could feel Steve’s cock hardening against his thigh. The hand on Tony’s ass pulled him down, grinding their bodies together.   

“Fu-uck me...” Tony groaned. 

Steve hummed through a moan, rolling them both over. He gathered both Tony’s wrists in one hand, pressing them against the mattress above Tony’s head. He rolled his hips down against Tony’s to hear him groan again. 

“Tell me, sweetheart, tell me what you want me to do to you.” Steve’s voice was low, steady. “Look at me.” Tony’s eyes were closed, but he could feel Steve’s stare. As he opened his eyes, he saw the hair previously combed neatly has fallen from its uniform pull to the side and now sways in the gentle push of the air conditioning. “Good boy.” Tony let out a little moan, much to Steve’s satisfaction.  

“You want me to fuck you, Tony? How do you want it, baby? Rough, on your elbows and knees? Want me to bend you over and take you and leave bite marks across your shoulders, bruises on your hips?” Steve rolled his hips again, leaning in once again for a kiss. This time, it was fast, sloppy, and he took his time sucking and biting on Tony’s bottom lip before continuing to speak. Tony was blushing and eyes hazy already.  

“Or do you want it slow? Soft, sweet? Want the sap of lovemaking? Staring into each other's eyes as I make you come on my cock?” Steve’s voice waivered when Tony whined, arching his back and rolling his hips up for friction against Steve. “Impatient, sweetheart? Shh... I’ll take care of you, don’t you worry.”  

Tony felt a fresh rush of heat in his cheeks again and he opened his eyes wide again, watching Steve’s expression. The blonde’s gaze was steady, eyes warm like his voice, lips soft, grip on Tony’s wrists hard as he wriggled them to test Steve. He sighed happily as he was still trapped by the man’s large hand.  

“Say it, Tony. Tell me what you want.” Steve ordered again. 

Tony wordlessly whined, mouth falling open, wanting to demand that Steve fuck him already. He didn’t care how, he just needed it. It dawned on Tony how long it had actually been since Tony had been fucked. His mouth watered, suddenly felt empty, missing something, as he thought of how to phrase his thoughts for Steve. 

“Fuck my mouth.” 

Tony mentally facepalmed himself. He had multiple degrees. He was a successful businessman. He certainly must have had picked up at least one or two social skills in his time on earth. Apparently, they didn’t extend to this situation – horny, deprived, and being straddled and dirty talked to by a blonde god.  

Steve grinned. “That can be arranged.”  


	2. The Sex, as Promised

**Summary for the Chapter:**

> The night continues.

**Notes for the Chapter:**

> Still unbeta'd, forgive any mistakessss

Steve’s jacket and clothing were left folded on the bedroom floor. He arranged Tony on his back, his head hanging off the edge of the mattress. Steve was holding two small bottles in front of Tony’s eyes, one red and one yellow.

“Strawberry.” Tony said, mouth left softly open, breathing deeply as he watched Upside Down Steve apply strawberry flavoured lube to his large cock.

Steve grinned when he saw Tony lick his lips. “Something big to stuff your big mouth with.”

Tony couldn’t stop the whimper that escaped his throat against his will. “You like that, sweetheart?” Steve’s left (dry) hand reached out to cup Tony’s stubbled cheek. His thumb crooked into the corner of Tony’s mouth and Tony turned into the pull, sucking like his life depended on it.

“Hold on, baby, the main course is still coming.” Steve teased, pulling his thumb away. He brought his hand down to support the back of Tony’s head.

Steve used his right hand to carefully line up the head of his cock between Tony’s lips. He moaned low as he felt Tony’s hot breath. Tony’s tongue reached out to taste test. The strawberry was strong and mouth-watering. Steve slowly pushed into Tony’s mouth, fingers curling gently into the short curls at the back of Tony’s neck.

The head of Steve’s cock was insistent on Tony’s tongue, a firm heat that he sucked on greedily, for just a moment, before Steve’s fingers tugged on his hair.

Tony did _not_ whine at the discouragement, did _not_ know why Steve chuckled before pushing further. Tony’s throat was full, stretching tightly around the hot intrusion. As Steve settled, Tony punched out a huff through his nose, closing his eyes. Steve’s balls were hairless, Tony noticed when the discomfort of pubes under (above?) his nose never came.

Steve gave the back of Tony’s neck gentle scritches while his other hand came down over Tony’s Adam’s apple. His fingers were still slick with strawberry lube, it smeared as Steve gently squeezed on both sides of his throat.

 _Fuck_ , Tony’s brain shorted out briefly. There was only the sound of Tony’s long yet shallow breaths.

“That’s right, sweetheart, get used to this.” Tony managed to squeak out a moan around Steve’s cock. “You’re gonna be feelin’ me til next week.”

At that, Steve gave a shallow thrust before pulling out until just the head of his cock was cradled between Tony’s lips. Tony’s tongue licked across the head quickly, catching the salty taste, before Steve started up a steady rhythm.

The rush of heat to his lips, blush on his cheeks, and coiling heat deep in his gut had Tony reaching for his cock. Why hadn’t he gotten his pants off, again? The shirt had to stay on for the atmosphere to remain sexy but damn did Tony regret not unzipping when he still had the chance to look at what he was doing. Just as his fingers slipped below his belt, his wrist was tugged away roughly.

“Nuh uh, I don’t think so.” Steve growled, bringing Tony’s leftt hand to hold the back of Steve’s thigh. His thrusts were steady, harsh, Tony’s breath quivering. “‘s that why you didn’t want rope just yet?” Steve clucked his tongue in disapproval. Tony’s moaned response was punctuated by Steve’s cock tapping the back of his throat in quick succession. “Sneaky boy you are.” Tony’s right hand was taken to Steve’s thigh too. “Hands stay there. That’s your final warning.”

_Mean Steve._

Tony groaned weakly. His cock ached and his grip on Steve’s thighs tightened as he fought his urge to stroke himself over his pants.

Everything became a haze as Tony focused dreamily on the fullness of his mouth, the pounding on the back of his throat, the taste of bitter precome and sweet strawberries. The hair at the nape of his neck was fisted tightly once again and Steve’s thrusts halted, his cock lodged fully in Tony’s wet heat. Tony swallowed around him desperately, relishing the weight of Steve’s cock in his mouth.

“Fuck, you want it that badly? Want me to shoot down your throat, Tony?” Tony’s fingernails pinched into the skin on Steve’s thighs, holding him close.

Steve’s cock pulsed as he came down Tony’s throat. Tony held his breath and swallowed earnestly, long after Steve was spent.

“Good boy…” Steve whispered, stroking Tony’s hair as his cock was sucked clean. “Come on, now. Let’s get you lying down properly.”

Tony gave an offended look to Steve when he removed Tony’s hands from his thighs and pulled out of Tony’s mouth. He pulled Tony’s shoulders up and nudged him to the center of the bed, setting his head on one of the lush pillows.

One hand found the top button on Tony’s dress shirt and Tony’s breath hitched. He grabbed Steve’s wrist and shook his head. Steve wordlessly lowered his hand to Tony’s belt buckle instead.

“Your poor cock has been ignored all night.” Steve said as he unbuckled and unzipped. “You have been such a good cockslut, let’s give it a little reward, shall we?”

Steve looked up to meet Tony’s eyes, watching for cues, consent. Tony’s throat was raw, eyes glazed, mouth pink and lips swollen. He looked well-fucked and he took a deep breath before nodding quietly.

Steve lifted Tony’s hips with ease to tug his pants and boxers down. Tony’s cock bobbed freely, hard and dark red from waiting. Steve’s warm fingers wrapped around the base, his hands were so large only the head was exposed above his grip. A small whimper escaped Tony’s lips at the touch, his hips jerked up. Steve made himself comfortable between Tony’s legs, spreading the brunet’s knees and running his left hand along Tony’s inner thigh. Tony shivered at the touch.

A gentle stroke of Tony’s cock spread the beading precome over his head. Steve watched Tony’s hands clench and unclench at his sides, fidgeting with the hem of his shirt. “Hands over your head, sweetheart. Hold the headboard.”

Tony obeyed, eyes boring into Steve’s as he gripped the edge of the headboard behind him.

“Good boy.”

The slick grip on Tony’s cock started stroking again, slow and languid. Tony huffed, eyes closed, hips jerking upwards. “I—” He cut himself off when he felt a slick finger rub at his hole. “N—f-fuck.”

“That feel good, baby? You want it?” Steve’s voice was low, weighing Tony down to the present. He nodded quickly. “Did I fuck the words out of your head? Where are your manners, sweetheart?”

Tony’s blush was fierce, hot on his cheeks and spreading down his neck. His eyes closed tighter, as though he had to fight to find words. No, _because_ he had to fight to find words. This was good. This was very good. His head was floating but his body was held in Steve’s strong hands. But Steve demanded words. Tony groaned and he worked to find them.

“P-please.” He managed to utter, opening his eyes to risk a glance at Steve’s face.

Tony was rewarded with a smile and there was a ping of relief rushing through him.

“You’re such a good boy, Tony. Raised well to say ‘please’ and ‘thank you’, weren’t we?” Steve continued to stroke Tony’s cock with his right hand while his left index gently pushed into Tony’s hole. Tony nodded steadily, agreeing with whatever it was that got Steve’s thick fingers inside him.

Soon there were two fingers inside him, gently pushing and stretching and then _yes, right there!_

“I’m—” Tony moaned.

“I know, Tony, I know, come for me. You look so fucking gorgeous, I wanna see what you look like when you’re coming.” Steve’s words were kindle to the fire of Tony’s arousal, sending shivers down his spine and waves of need to his cock.

Tony came with a shout and his arms were shaking before they fell from their position above his head, from holding the headboard. They felt like jelly and he relished the aftershocks of his orgasm.

“That was so good.” Steve whispered into his ear. When did he crawl over Tony?

Thankfully, Steve did not settle on Tony’s chest to hold him. He rolled to the side and propped himself up on one elbow to stroke Tony’s hair. Tony did _not_ hum blissfully.

“Do you want the first shower?” Tony asked.

Steve snorted. “Out of the two of us, I think you’re the one who needs the shower.”

After taking a moment to process that _unprovoked sass_ , Tony chuckled. “You’ve got a point.”

Tony stretched out his limbs across the mattress before picking himself up off the bed. He gathered a set of silk pajamas from his closet before heading to the en suite bathroom.

The shower was hot and soothing on Tony’s limbs, his arms pleasantly ached. He breathed deeply as he tapped on the arc reactor. He stepped out of the spray and dried himself off with a lush towel. With a fresh folded towel, he emerged from the bathroom dressed for sleep, but he was feeling restless.

Steve was still laid out on the bed, arms stretched with his hands folded under his head, eyes closed.

“Your turn.” Tony said, setting the clean towel next to Steve’s hip.

Peeking out of one eye, Steve looked at Tony and smiled. “Nice PJs.”

“You jealous? Maybe next time I’ll lend you some, but since I paid for the overnight, I’ll get my money’s worth of your ridiculous body.” Tony meant to be playful, but it sounded more crude than anything. He would have never said that if it were a woman laying on his bed.

“Fuck, sorry, I didn’t—That’s not cool, I—”

Steve raised his hand as he sat up. “Don’t worry about it. I’ll go shower. Lie down.”

Tony sighed as he heard the bathroom door close behind him. He didn’t feel ready for sleep just yet, but he got comfortable nonetheless. He slipped under the sheets and he listened to the sound of the water running in the next room.

He must have dozed off, because he opened his eyes to see Steve climbing onto the mattress. He still shone a little from the shower, but he didn’t drip. His hair appeared towel-dried and tousled in a way that Tony wanted to have done himself. Tony’s eyes travelled down the stretch of Steve’s neck, across his bare broad shoulders. He was tempted to bite down onto Steve’s neck once he got within range. Steve’s chest and abs were absolutely delicious, and as Tony found his way down to Steve’s flaccid cock, his mouth practically watered.

Tony winced inwardly. _Keep it together, Stark._

“Enjoying the view?” Steve teased, climbing onto the bed but not pulling up the sheets over his body. Tony licked his lips.

“You’re gorgeous.”

“You’re not too bad yourself.”

There was a moment of silence. Steve decided to pull the sheets up over his lap.

“So…”

“So…?” Tony repeated.

“I assumed you wanted me to sleep in here. Did you have a setup in mind, or…?” Steve trailed off, gesturing with open palms.

Tony shrugged. “Cuddling?” He worked hard to develop this leveled tone for when he asked to cuddle with his escorts.

Steve cocked one eyebrow. “You a little spoon?”

“Excuse me, don’t think that just because I’m shorter than you automatically makes me the little spoon here. I could challenge stereotypes! Overcome the ideas of what a subby dude is ‘supposed’ to want or like, and—fuck, yeah I’m a little spoon.” Tony turned over on his side, back facing Steve. He looked over his shoulder expectantly.

Steve was dumbstruck for a quick second, then giddily curled up around Tony’s back. He draped his leg over Tony’s hips and held him close. “Good?”

Tony nodded. “Good.”

 

Tony hadn’t fallen asleep so fast in months. When he awoke, JARVIS informed him it was 10:31am. Tony had one arm splayed out onto the mattress behind him.

Steve was already gone.

*

  

 

 

 

> SUBJECT: Escort Service Post-Appointment Receipt
> 
> FROM: V.P. Escorts
> 
> TO: Tony Stark
> 
>  
> 
> _Escort ID: 72091_
> 
>  
> 
> _Activities Conducted: Sexual Contact*, Biting, Dominance*_
> 
>   * _Sexual Contact: Oral Sex, Sexual Fluid Exchange, Anal Sex_
>   * _Dominance: Humiliation, Hair Pulling_
> 

> 
> _Special requests: Overnight Stay, Alcohol Consumption_
> 
>  
> 
> **Scheduled: 2/20/2019 9:00pm - 2/21/2019 9:00am**
> 
>  
> 
> _Above transaction record confirmed by 71091 at 9:05am 2/21/2019._

*

 

 

 

 

> SUBJECT: Escort Service Reservation Confirmation
> 
> FROM: V.P. Escorts
> 
> TO: Tony Stark
> 
>  
> 
> _Escort Request: 72091_
> 
>  
> 
> _Dress Code: [n/a]_
> 
> _Activity Requests: Sexual Contact*, Rope Usage, Biting, Dominance*,  Exhibitionism, Role Play_
> 
>   * _Sexual Contact: Frottage, Oral Sex, Anal Sex, Sexual Fluid Exchange, Anal Toys, Rimming, Face-Fucking, Orgasm Delay, Deepthroating, Somnophilia, Rough Sex*, Object Insertion, Wall Sex_
>   * _Dominance: Humiliation, Hair Pulling, Spanking, Gagging, Leashes, Collars, Spreader Bars, Orgasm Denial, Forced Orgasm, Body Worship, Asphyxiation_
>   * _Rough Sex subject to increased evening fee._
> 

> 
> _Special requests: Overnight Stay, Alcohol Consumption, Rough Sex*_
> 
>  
> 
> **Scheduled: Reservation pending escort’s availability**
> 
> REPEAT ESCORT (1) EVENING =   $1500.00
> 
> SPEC REQUEST =   $900.00
> 
> SPEC REQUEST =   $500.00
> 
> SUBTOTAL = $2900.00
> 
> TAXES =   $435.00
> 
> TOTAL TO CREDIT CARD = $3335.00
> 
> _All service requests are subject to the judgment and final decision of Escort Commissioned, in accordance with the_ Sex Workers Protections Act _. Billing disputes must be taken to our Customer Service department. Contact information is listed at the bottom of this email and on our website._

**Notes for the Chapter:**

> Tony is really intent on the next appointment. Steve will be like wtf


End file.
